At Roofr, we’re obsessed with our customers. We constantly gather feedback to shape, prioritize, and launch the products they truly need. That’s what makes Roofr’s CRM special. We started by building essential sales tools like aerial roof measurements and digital sales proposals. But when our customers asked for a simple, affordable way to manage and scale their entire businesses, we listened. So, we created a CRM that connects these solutions—along with payments, material ordering, and more—into a seamless, powerful platform. With a clear roadmap ahead, we’re excited to continue expanding and leading the market with innovative products.
We have an amazing culture, strong financials, and best-in-class company metrics. It’s an exciting time to be part of an extraordinary startup that is already successful, yet still early enough to offer its team significant growth, equity, and the opportunity to make a real impact.
As the Director of Customer Success, you will oversee Account Set-up (Builds), Implementation, Onboarding, Retention, Customer Education and Customer Insights. You’ll be responsible for designing and scaling processes, playbooks, and strategies that ensure customers achieve measurable value quickly and continue to grow with us. This is a hands-on leadership role where you’ll both build the foundation for Customer Success at scale and directly coach and develop a growing team.
What You’ll Get to Do:- Leadership & Strategy
- Define and execute the vision, strategy, and operating model for Customer Success across Builds, Implementation, Onboarding, Retention, Customer Education and Customer Insights functions.
- Build, mentor, and inspire a high-performing CS team while fostering a customer-centric culture.
- Partner closely with Growth, Product, Sales, Support, Partnerships and Marketing to align on customer journey, feedback loops, and GTM strategy.
- Account Set-up (Builds)
- Manage the Build Manager, responsible for Offshore Shift Leads, and Offshore Builders.
- Ensure accurate and scalable execution of customer account setup, account optimization and data migration.
- Expand Builder responsibilities to support growth in new products, increased self-serve demand, and migration work.
- Maintain round-the-clock coverage through offshore teams and shift leads.
- Implementation & Onboarding
- Oversee Managers of Customer Onboarding (Greenfield, Brownfield, and Field) and Implementation Specialists, ensuring consistent, high-quality onboarding experiences across all customer segments.
- Design scalable onboarding frameworks to reduce time-to-value and set customers up for long-term success.
- Create and refine implementation playbooks that not only drive adoption but also surface upsell and cross-sell opportunities as customers expand their usage.
- Customer Education
- Oversee Customer Education; training programs, persona-based enablement, virtual and in-person onboarding, and scaling Roofr Academy content.
- Ensure adoption across self-serve and sales-assisted customers through structured education programs that support both admins and end-users.
- Retention & Growth
- Establish metrics, processes, and playbooks to increase retention and reduce churn.
- Develop and optimize health scoring models to identify risks and opportunities across the customer base.
- Build proactive retention strategies, including customer engagement and success planning.
- Design churn-save playbooks that systematically identify at-risk accounts, outline intervention strategies, and generate pipeline for upsells, cross-sells, and increased adoption.
- Operations & Scale
- Translate customer insights into actionable initiatives across Product, Marketing, and Revenue.
- Build systems, processes and playbooks that support customer success across self-serve, sales assisted and sales lead customers at scale.
- Define key success metrics and provide executive-level reporting on onboarding & implementation, adoption, retention, education, customer insights and customer experience.
- Standardize playbooks and best practices across all CS functions.
- Drive operational planning for headcount, ramp time, and resource allocation based on subscription growth.
- 8+ years of Customer Success experience, with at least 3+ years leading CS teams in B2B SaaS with both self-serve and sales-assisted motions.
- Proven track record scaling CS organizations in early-stage to growth-stage startups.
- Strong background in PLG environments, with experience aligning CS motions to both self-serve and sales-assisted journeys.
- Excellent leadership, coaching, and people-development skills.
- Highly operational, with proven ability to build scalable systems, playbooks, and processes that enable consistent execution across teams.
- Strong analytical mindset with the ability to translate data into strategy & decisions.
- Exceptional cross-functional collaboration skills, especially with Product, Sales, and Marketing.
- Passionate about delivering an outstanding customer experience and building long-term relationships.
- Aptitude for quickly learning and adapting to new technologies, tools, and systems.
- Exceptional communication skills, with the ability to distill complex concepts into clear, actionable narratives for diverse audiences.
🏠 What we offer (US + Canada)
When you join our team, you’re not just accepting a job. You’re making a career move. Here’s how we’ll support you in doing some of the most impactful work of your career:
🏝️ Vacation/Paid Time Off:
- 1st week of employment is mandatory PTO! Start your journey with Roofr by decompressing and recharging - we will see you in week 2!
- 1 Friday off per month (we call those our laundry days!)
- Company wide paid shutdown for the week between Christmas and New Years
- Flexible time off
- 80% employer paid benefits
- RRSP/401k match
- Generous Parental Leave policy
🤝 Perks:
- We host 2 retreats per year and great team building activities
- Ample learning and development opportunities to continue growing your career
- Home office setup stipend
- Internet and phone allowance
- Remote first culture
- Weekly Friday paydays!
🤖 AI Notice
At Roofr, we’re big fans of AI. It helps us write job descriptions that don’t put you to sleep, takes notes during interviews so we can actually listen, and even helps us track down awesome humans like you.
Feel free to use AI to prep, research, or get pumped up for your interview (we see you, ChatGPT power users 👀). But when it’s time to chat, we’d love to meet you, not your AI alter ego. Bring your real, unfiltered self, we promise we will too.
And don’t worry, a real, live human is behind every part of our process. Every application is reviewed by a real person, and you’ll always speak with real humans throughout the interview process. No bots, just good people ☺️
⚠️ Important Notice
We’ve been made aware of an individual impersonating Roofr using a fraudulent domain: roofrr.com (note the extra “r”). Our company takes the security and privacy of job applicants very seriously. We will never ask for payment, bank details, or personal financial information as part of the application process. All our legitimate job postings can be found on our official career site. Please be cautious of job offers that come from non-company email addresses, instant messaging platforms, or unsolicited calls.
To ensure your application is legitimate, please apply directly through our official careers page: https://roofr.com/careers.
If you receive any suspicious messages or have questions, reach out to us at [email protected].
Your safety and security are important to us — thank you for your vigilance!
Roofr is proud to be an equal opportunity employer. We are committed to equal employment opportunity in the workplace regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or veteran status.
